EP1366746B1 - Shampooing contenant au moins une silicone et au moins un copolymère linéaire séquencé amphiphile, anionique ou non-ionique - Google Patents

Shampooing contenant au moins une silicone et au moins un copolymère linéaire séquencé amphiphile, anionique ou non-ionique Download PDF

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Publication number
EP1366746B1
EP1366746B1 EP03291168A EP03291168A EP1366746B1 EP 1366746 B1 EP1366746 B1 EP 1366746B1 EP 03291168 A EP03291168 A EP 03291168A EP 03291168 A EP03291168 A EP 03291168A EP 1366746 B1 EP1366746 B1 EP 1366746B1
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EP
European Patent Office
Prior art keywords
composition according
washing composition
alkyl
anionic
water
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
EP03291168A
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German (de)
English (en)
French (fr)
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EP1366746A1 (fr
Inventor
Claude Dubief
Serge Restle
Franck Giroud
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LOreal SA
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LOreal SA
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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A61K8/89—Polysiloxanes
    • A61K8/896—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate
    • A61K8/898—Polysiloxanes containing atoms other than silicon, carbon, oxygen and hydrogen, e.g. dimethicone copolyol phosphate containing nitrogen, e.g. amodimethicone, trimethyl silyl amodimethicone or dimethicone propyl PG-betaine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/90—Block copolymers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/02—Preparations for cleaning the hair
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/12—Preparations containing hair conditioners
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/59—Mixtures
    • A61K2800/594—Mixtures of polymers

Definitions

  • the present invention relates to compositions for washing keratinous fibers containing, in a base for shampoos, at least one linear amphiphilic block copolymer, anionic or nonionic, comprising at least one hydrophobic block and at least one hydrophilic block, and at least one non-volatile silicone.
  • Nonvolatile silicones have long been known in the cosmetics field, and in particular in the hair field, for their conditioning properties. Indeed, they facilitate the disentangling of the hair and give them a smooth and shiny appearance. These conditioning performance of silicones, satisfactory on normal hair, are however significantly less on hair sensitized by treatments that may degrade the structure of the hair such as oxidative coloring or discoloration and permanent deformation. However, it is precisely the hair damaged by these treatments that have problems of disentangling and cosmetic defects that would require a conditioning effect.
  • the Applicant has surprisingly found that the use of a group of particular linear amphiphilic block copolymers in combination with at least one silicone, in a particular base for shampoos, made it possible to solve the problems of the prior art.
  • the shampoos developed by the applicant facilitate the disentangling in the wet state and in the dry state of the hair and give excellent cosmetic results, that is to say, give the hair a shiny appearance and a silky touch while by giving them body and support, and this as well on natural hair as on hair moderately or heavily damaged.
  • the present invention also relates to the use of such a composition for washing keratinous fibers.
  • linear block copolymers that may be used according to the present invention are so-called “amphiphilic” copolymers, namely copolymers comprising at least one hydrophobic block and at least one hydrophilic block.
  • hydrophobic block according to the present invention a block comprising at least 75 mol% of water-insoluble monomers and "hydrophilic block", a block comprising at least 75 mol% of water-soluble monomers.
  • Water-soluble monomers forming the hydrophilic block (s) of the block copolymers used in the present invention may be of anionic or nonionic nature and may be used alone or as a mixture containing two or more different monomers.
  • water-soluble anionic monomers are ethylenically unsaturated carboxylic acids, such as acrylic acid, methacrylic acid, itaconic acid, fumaric acid, crotonic acid and acid. maleic acid, 2-acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, vinylsulfonic acid and vinylphosphonic acid.
  • carboxylic acids such as acrylic acid, methacrylic acid, itaconic acid, fumaric acid, crotonic acid and acid.
  • maleic acid 2-acrylamido-2-methylpropanesulfonic acid, styrenesulfonic acid, vinylsulfonic acid and vinylphosphonic acid.
  • the nonionic water-soluble monomers include, inter alia, acrylamide, N-alkylated acrylamides, C 1-6 alkyl or N, N-di-C 1-3, polyethylene glycol acrylate, polyethylene glycol methacrylate, N -vinylacetamide, N-methyl-N-vinylacetamide, N-vinylformamide, N-methyl-N-vinylformamide, N-vinyllactams having a cyclic group of 4 to 9 carbon atoms, vinyl alcohol (copolymerized in the form of vinyl acetate then hydrolyzed), ethylene oxide, hydroxyethyl acrylate, hydroxypropyl acrylate, hydroxyethyl methacrylate and hydroxypropyl methacrylate.
  • the water-insoluble monomers forming the hydrophobic block or blocks of the block copolymers are preferably chosen from vinylaromatic monomers such as styrene and its alkylated derivatives, such as 4-butylstyrene, ⁇ -methylstyrene and vinyltoluene, and dienes such as butadiene and 1,3-hexadiene, and alkyl derivatives of dienes such as isoprene and dimethylbutadiene, chloroprene, C 1-10 alkyl acrylates, C 6-10 aryl or aralkyl C 6- 10 alkyl methacrylates and C 1-10 aryl, C 6-10 aralkyl or C 6- 10, such as methyl (meth) acrylates, of ethyl, n-butyl, 2-ethylhexyl, tert-butyl, isobornyl, phenyl or benzyl, vinyl acetate, vinyl ethers of formula CH 2
  • the water-soluble monomers and the water-insoluble monomers represent at least 75 mol% respectively of the hydrophobic and hydrophilic blocks.
  • the hydrophobic block (s) can comprise up to 25 mol% of one or more water-soluble monomers. This proportion is preferably at most 10 mol% and, ideally, less than or equal to 5 mol%.
  • the hydrophilic block (s) may comprise up to 25 mol%, preferably up to 10 mol%, and most preferably up to 5 mol%, of one or more insoluble monomers in the water.
  • linear block copolymers used also naturally include those in which the hydrophilic blocks and the hydrophobic blocks consist exclusively of water-soluble monomers and water-insoluble monomers, respectively. These blocks can be homopolymeric blocks or copolymer blocks containing two or more different monomers of the same type.
  • the average molecular weight of each block is preferably between 500 and 100 000, especially between 500 and 50,000, with a polydispersity index (M w / M n ) between 1.01 and 3.0, preferably between 1.1 and 2.5.
  • the block polymers of the invention may be prepared by the synthesis methods conventionally used to obtain block polymers. Examples that may be mentioned are anionic or cationic polymerizations and controlled radical polymerization (see “New Method of Polymer Synthesis", Blackie Academic & Professional, London, 1995, Volume 2, page 1 , or Trends Polym. Sci. 4, page 183 (1996) by CJ Hawker ), which can be implemented different processes such as, for example, radical atom transfer polymerization (Atom Transfer Radical Polymerization or ATRP) (see JACS, 117, page 5614 (1995), by Matyjasezwski et al. ), the radicals method such as nitroxides ( Georges et al., Macromolecules, 1993, 26, 2987 ). These methods can also be used to obtain only one of the two types of blocks of the polymer of the invention, the other block being introduced into the final polymer via the initiator used or by coupling reaction between the blocks. hydrophilic and hydrophobic.
  • the washing compositions of the present invention may contain the block copolymers in the dissolved or dispersed state, and these copolymers are therefore preferably soluble or dispersible in the cosmetic medium used.
  • the diblock copolymers are preferably water-soluble.
  • Water-soluble is understood to mean compounds (polymers or monomers) which, introduced into water at 25 ° C., and if necessary neutralized, at a concentration by weight equal to 0.1%, make it possible to obtain a solution or a macroscopically homogeneous and transparent suspension, i.e. having a light transmittance value, at a wavelength of 500 nm, through a 1 cm thick sample, at least 70%, preferably at least 80%.
  • the washing compositions of the present invention comprise - in addition to the block copolymer (s), amphiphilic, anionic or nonionic, described above - at least one non-volatile silicone at room temperature, which is generally present in a concentration of between 0.01 and 20%, based on the total weight of the washing composition.
  • non-volatile silicone in the sense of the present invention any silicone whose boiling temperature is greater than 245 ° C at atmospheric pressure.
  • the silicones that can be used in accordance with the invention may be soluble or insoluble in water or in the composition. This is particularly polyorganosiloxanes which are insoluble in water and in the composition and which are in the form of oils, waxes, resins and silicone gums.
  • the silicones that can be used in the washing compositions can be crosslinked or non-crosslinked, organomodified or otherwise.
  • water-insoluble silicones and in the composition are meant those having a solubility, measured at 25 ° C., of less than or equal to 0.1% by weight in water or in the composition, that is to say that beyond this concentration, they do not form transparent isotropic solutions.
  • Organopolysiloxanes are defined in more detail in Walter NOLL “Chemistry and Technology of Silicones” (1968) Academy Press .
  • the non-volatile silicones are preferably polyalkylsiloxanes, polyarylsiloxanes, polyalkylarylsiloxanes, silicone gums and resins, polyorganosiloxanes modified with organofunctional groups, and mixtures thereof.
  • silicones are more particularly chosen from polyalkylsiloxanes, among which, for example, polydimethylsiloxanes containing trimethylsilyl end groups having a viscosity of 5 ⁇ 10 -6 to 2.5 m 2 / s at 25 ° C. and preferably 1 ⁇ 10 -5 to 1 m 2 may be mentioned. / s.
  • the polyalkylarylsiloxanes are especially chosen from polydimethyl methylphenylsiloxanes and linear and / or branched polydimethyl diphenylsiloxanes with a viscosity of from 1 ⁇ 10 -5 to 5 ⁇ 10 -2 m 2 / s at 25 ° C.
  • the silicone gums that can be used in accordance with the invention are in particular polydiorganosiloxanes having high average molecular weights of between 200,000 and 1,000,000 used alone or in a mixture in a solvent.
  • This solvent may be chosen from volatile silicones, polydimethylsiloxane (PDMS) oils, polyphenylmethylsiloxane (PPMS) oils, isoparaffins, polyisobutylenes, methylene chloride, pentane, dodecane, tridecanes or mixtures thereof.
  • organomodified silicones that may be used in accordance with the invention are silicones as defined above and comprising, in their structure, one or more organofunctional groups attached via a hydrocarbon radical.
  • grafted silicone polymers are in particular polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene type connection link, mixed polymeric units of the poly (meth) acrylic acid and poly type. alkyl (meth) acrylate and polydimethylsiloxanes (PDMS) on which are grafted, via a thiopropylene type connecting link, polymeric units of the poly (meth) acrylate isobutyl type.
  • PDMS polydimethylsiloxanes
  • PDMS polydimethylsiloxanes
  • all the silicones can also be used in the form of emulsions.
  • the combination of the two types of polymers essential for the present invention described above is in a specific shampoo base containing the combination of at least one anionic surfactant and at least one nonionic surfactant and / or at least one amphoteric surfactant.
  • anionic, nonionic and amphoteric surfactants that can be used in the washing compositions of the present invention are known and commonly used in the cosmetics field.
  • alkali metal salts such as sodium salts, ammonium salts, amine salts, aminoalcohol salts or the salts thereof.
  • alkaline earth metal salts for example, of magnesium, of the following types: alkyl sulphates, alkyl ether sulphates, alkyl amido ether sulphates, alkyl aryl polyether sulphates, monoglyceride sulphates; alkylsulfonates, alkylamidesulfonates, alkylarylsulfonates, ⁇ -olefin-sulfonates, paraffin-sulfonates, alkylsulfosuccinates, alkylethersulfosuccinates, alkylamidesulfosuccinates, alkylsulfoacetates, acylsarcosinates and acylglutamates, the alkyl
  • alkyl monoesters of C 6-24 of polyglycoside dicarboxylic acids such as alkyl glucoside citrates, polyglycoside tartrates and alkyl polyglycoside alkyl sulphosuccinates, alkylsulphosuccinamates, acylisethionates and N-acyltaurates, the alkyl or acyl group of all these compounds having from 12 to 20 carbon atoms.
  • anionic surfactants that can be used in the compositions of the present invention is that of acyl lactylates, the acyl group of which contains from 8 to 20 carbon atoms. Furthermore, it may also be made of alkyl-D-galactoside-uronic acids and their salts as well as polyoxyalkylenated (C 6-24) ether carboxylic acids, polyoxyalkylenated (C 6-24) aryl (C 6-24 polyoxyalkylenated ether carboxylic acids, polyoxyalkylenated (C 6-24 ) amidoether carboxylic acids and their salts, in particular those containing from 2 to 50 ethylene oxide units, and mixtures thereof.
  • Alkyl sulphates, alkyl ether sulphates and alkyl ether carboxylates, and mixtures thereof, are preferably used, in particular in the form of alkali metal or alkaline earth metal salts, ammonium, amine or aminoalcohol.
  • nonionic surfactants that can be used in the compositions of the present invention are compounds that are well known per se (see in particular in this regard " Handbook of Surfactants "by MR PORTER, Blackie & Son editions (Glasgow and London), 1991, pp 116-178 ). They are chosen in particular from alcohols, alpha-diols, alkyl (C 1-20 ) phenols or polyethoxylated, polypropoxylated or polyglycerolated fatty acids, having a fatty chain comprising, for example, from 8 to 18 carbon atoms, the number of ethylene oxide or propylene oxide groups that can range from 2 to 50 and the number of glycerol groups ranging in particular from 2 to 30.
  • the condensates of ethylene oxide and of propylene oxide on fatty alcohols preferably having from 2 to 30 ethylene oxide units, the polyglycerolated fatty amides comprising on average from 1 to 5 glycerol groups and in particular from 1.5 to 4, the fatty acid esters of sorbitan ethoxylates having from 2 to 30 ethylene oxide units, sucrose fatty acid esters, polyethylene glycol fatty acid esters, (C 6-24 ) alkyl polyglycosides, N- (alkyl) derivatives, C 6-24 ) glucamine, amine oxides such as (C 10-14 ) alkyl amines or N- (C 10-14 acyl) aminopropylmorpholine oxides.
  • the nonionic surfactants mentioned above the (C 6-24 alkyl) polyglycosides are preferably used.
  • the amount of anionic surfactants is preferably from 3% to 35% by weight, in particular from 5% to 25% by weight, based on the total weight of the cosmetic composition.
  • the total amount of amphoteric and / or nonionic surfactants is preferably between 0.5 and 30%, and in particular between 1 and 20% relative to the total weight of the composition.
  • the pH of the compositions of the present invention is preferably between 2 and 11, and in particular between 3 and 10.
  • the liquid medium of the compositions of the invention is aqueous or aqueous-alcoholic, that is to say that, in the latter case, the compositions contain in addition to an aqueous phase, one or more solvents chosen from lower alcohols such as ethanol or isopropanol, and polyols such as glycerol, propylene glycol and polyethylene glycols.
  • compositions according to the invention may also contain cosmetic active ingredients or formulation additives such as anionic, nonionic, cationic or amphoteric film-forming polymers, natural or synthetic, anionic, amphoteric, zwitterionic, nonionic or cationic polymeric thickeners , associative or not, nonpolymeric thickeners such as acids or electrolytes, cationic surfactants, pearlescent agents, opacifying agents, dyes or pigments, perfumes, mineral, vegetable and / or synthetic oils, waxes including ceramides, vitamins, UV filters, anti-dandruff agents, anti-doping agents, -radicals, plasticizers, preservatives or pH stabilizers.
  • cosmetic active ingredients or formulation additives such as anionic, nonionic, cationic or amphoteric film-forming polymers, natural or synthetic, anionic, amphoteric, zwitterionic, nonionic or cationic polymeric thickeners , associative or not, nonpolymeric thickeners
  • A (according to the invention) B (comparative) C (comparative) anionic surfactant (a) 17% 17% 17% amphoteric surfactant (b) 2.5% 2.5% 2.5% diblock copolymer PS-b-POE (c) 0,5% - - PEO-b-PPO diblock copolymer (d) - - 0,5% amodimethicone (e) 1% 1% 1% water qsp 100% qsp 100% qsp 100% qsp 100% (a) sodium lauryl ether sulphate (2 EO) (b) Cocoyibetaine (c) poly (styrene-b-ethylene) diblock copolymer sold under the name Tegomer® SE 1010 by the company GOLDSCHMIT (d) block copolymer poly (ethylene oxide-b-propylene oxide) sold under the name Synperoic PE / F 127 by the company ICI (e) DC 939, Dow Chemical

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
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  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
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EP03291168A 2002-05-31 2003-05-20 Shampooing contenant au moins une silicone et au moins un copolymère linéaire séquencé amphiphile, anionique ou non-ionique Expired - Lifetime EP1366746B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR0206732A FR2840206B1 (fr) 2002-05-31 2002-05-31 Shampooing contenant au moins une silicone et au moins un copolymere lineaire sequence amphiphile, anionique ou non- ionique
FR0206732 2002-05-31

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EP1366746A1 EP1366746A1 (fr) 2003-12-03
EP1366746B1 true EP1366746B1 (fr) 2010-04-14

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EP03291168A Expired - Lifetime EP1366746B1 (fr) 2002-05-31 2003-05-20 Shampooing contenant au moins une silicone et au moins un copolymère linéaire séquencé amphiphile, anionique ou non-ionique

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EP (1) EP1366746B1 (es)
JP (1) JP2004002425A (es)
AT (1) ATE464096T1 (es)
BR (1) BR0301525A (es)
DE (1) DE60332070D1 (es)
ES (1) ES2341326T3 (es)
FR (1) FR2840206B1 (es)
MX (1) MXPA03004747A (es)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7803877B2 (en) 2002-09-26 2010-09-28 L'oreal S.A. Block polymers and cosmetic compositions and processes comprising them
US7875265B2 (en) 2002-09-26 2011-01-25 L'oreal Cosmetic composition comprising a sequenced polymer and a plasticizer
US8119110B2 (en) 2003-09-26 2012-02-21 L'oreal S.A. Cosmetic composition comprising a block polymer and a non-volatile silicone oil
US8710152B2 (en) 2006-07-27 2014-04-29 L'oreal Block polymers and their process of preparation
US8728451B2 (en) 2004-03-25 2014-05-20 L'oreal Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof

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US7176170B2 (en) * 2002-05-31 2007-02-13 L'oreal Shampoo comprising at least one silicone and at least one anionic or nonionic, amphiphilic linear block copolymer
DE102004007473A1 (de) * 2004-02-13 2005-09-01 Basf Ag Mischung, umfassend ein Tensid und ein Cotensid
DE102004030885A1 (de) * 2004-06-25 2006-02-09 Henkel Kgaa Haarreinigungsmittel mit aminofunktionellen Siliconen

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Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7803877B2 (en) 2002-09-26 2010-09-28 L'oreal S.A. Block polymers and cosmetic compositions and processes comprising them
US7875265B2 (en) 2002-09-26 2011-01-25 L'oreal Cosmetic composition comprising a sequenced polymer and a plasticizer
US7915347B2 (en) 2002-09-26 2011-03-29 L'oreal S.A. Block polymers and cosmetic compositions and processes comprising them
US7932324B2 (en) 2002-09-26 2011-04-26 L'oreal Block polymers and cosmetic compositions and processes comprising them
US8992903B2 (en) 2002-09-26 2015-03-31 L'oreal Composition comprising at least one block polymer and at least one gelling agent
US9017704B2 (en) 2002-09-26 2015-04-28 L'oreal Composition comprising a block polymer and a film-forming agent
US8119110B2 (en) 2003-09-26 2012-02-21 L'oreal S.A. Cosmetic composition comprising a block polymer and a non-volatile silicone oil
US8728451B2 (en) 2004-03-25 2014-05-20 L'oreal Styling composition comprising, in a predominantly aqueous medium, a pseudo-block polymer, processes employing same and uses thereof
US8710152B2 (en) 2006-07-27 2014-04-29 L'oreal Block polymers and their process of preparation

Also Published As

Publication number Publication date
FR2840206B1 (fr) 2005-08-05
ATE464096T1 (de) 2010-04-15
BR0301525A (pt) 2004-09-08
EP1366746A1 (fr) 2003-12-03
FR2840206A1 (fr) 2003-12-05
DE60332070D1 (de) 2010-05-27
MXPA03004747A (es) 2005-02-14
ES2341326T3 (es) 2010-06-18
JP2004002425A (ja) 2004-01-08

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